Cheap Flights from Chicago to Key West
Cheap Flights from Chicago to Key West
Looking for cheap flights from Chicago to Key West? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Key West vary by season, cabin, and date, but available award flights can start around 7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Key West for specific travel dates.
2026-11-06
ORD - EYW
Economy | Non stop | 5 left
From 7,500 Pts + $25.6
2026-11-08
ORD - EYW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
ORD - EYW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - EYW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-15
ORD - EYW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-16
ORD - EYW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Key West flight facts
Distance
1,249 mi
2,011 km in a straight line
Estimated flight time
about 3h
In the air, for the straight-line distance
Time difference
+1h
Key West is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Key West
EYW · Key West Intl
Nearby airport alternatives
Flights Chicago - Miami · Miami is 125 mi from Key West
Flights Chicago - Fort Myers · Fort Myers is 137 mi from Key West
Flights Chicago - Fort Lauderdale · Fort Lauderdale is 145 mi from Key West
Flights Indianapolis - Key West · Indianapolis is 174 mi from Chicago
Premium cabin flights from Chicago to Key West
Premium cabin
2026-11-17
ORD - EYW
First | Non stop | 6 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-22
ORD - EYW
First | 1 Stop | 5 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-23
ORD - EYW
First | 1 Stop | 1 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-07
ORD - EYW
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-13
ORD - EYW
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-14
ORD - EYW
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Key West depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Key West.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Key West.
Chicago and Key West are about 1,249 miles (2,011 km) apart in a straight line.
Flying the 1,249-mile straight-line distance takes about 3h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Key West is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Key West: Key West Intl (EYW).
Travelers searching this route also look at other popular routes into Key West, plus the return trip when we track it. Fares and award space change daily.
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